Pyridine → HCID 86739728, compound

HRID 1633175Notes

Reaction equation

HRID 1633175 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([O:19][CH3:20])[CH:3]=1.N1C=CC=CC=1.[O:27]=[P:28](Cl)([Cl:30])[Cl:29]>C(Cl)Cl>[CH2:11]([O:10][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][P:28]([Cl:30])([Cl:29])=[O:27])=[CH:3][C:4]=1[O:19][CH3:20])=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 12843952HCID 12843952, compound

Product 1

HCID 86739728HCID 86739728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl N-(4-amino-2-methoxyphenyl)carbamate (IV; X=PhCH2OCONH, R1 =OCH3) (20 g, 73.5 mM) in CH2Cl2 (25 mL) was added over 5 min to a stirred, icecold, mixture of dry pyridine (25 mL) and POCl3 (100 mL), and the resulting mixture was stirred below 5° C. for a further 2 h. Precipitation with petroleum ether (500 mL) at -10° C. for 15 h gave crude solid product, which was isolated by decantation and washed with two portions of petroleum ether.

Workup

  1. customPrecipitation with petroleum ether (500 mL) at -10° C. for 15 h
  2. customgave crude solid product
  3. customwhich was isolated by decantation
  4. washwashed with two portions of petroleum ether

Sources & evidence

ORD record
ord-842a4c693d8141898123e3914257df08
Source dataset
uspto-grants-1984_10
Patent number
US04479000

Reaction notes

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